
Vacation rentals with a pool in Windley Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Windley Key
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windley Key rentals with a pool
House rentals with a pool

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

Tiny Home on Waterfront | Bay Views | Deck | Pool

Paradise - Pool, Hot tub, Mini Golf, Dockage, Fish

Oceanfront with Pool near Sombrero Beach

Waterfront Home 37.5-ft dock, Cabana Club Included

Beach House, Private Pool & Dock, Gulf Sunset view

Escape to the Seaside!

CASA AZUL - The Salt Life Meets Luxury! Voted Best
Condo rentals with a pool

Your Happy Place - Oceanfront

2BR - Key Largo Sunshine Getaway

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Ocean Views at Ocean Pointe

Condo in the Keys, Peaceful ocean view retreat!

Ocean views at âSangria Sunriseâ 10% off Charters

Studio with Balcony, Kitchen, Open Living Space

Tropical Getaway
Other vacation rentals with a pool

Ocean View Duplex Penthouse | Pool | Vista Two

Newly Renovated Piece ofParadise

When Paradise is Key: Tropical Oceanfront Condo

Anglers Haven- 2 bed 2 bath home in Islamorada

Panoramic Ocean Views, Ocean Pointe Condo

The Keys Grand Blue/ 120'Dock/Mini Golf/ GameRoom

Mariners 212 Great Location with Marina Views

Gone Coastal @ Ocean Pointe
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- Rentals with pools Islamorada
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Cannon Beach
- Biscayne National Park
- Coral Castle
- Calusa Beach & Loggerhead Beach
- Cocoa Plum Beach
- Deering Estate
- Theater of the Sea
- Conch Key
- Everglades Alligator Farm
- Monkey Jungle
- Far Beach
- Horseshoe Beach
- Sea Oats Beach
- Long Key State Park
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Bahia Honda State Park
- Keys' Meads
- Schnebly Redland's Winery & Brewery
- Sandspur Beach